Sort by
Relevancy

Free Stories

100%
I Give Up
The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... Read full Story
ASSEaster5678 2018-09-14 9,082 Cumshot Bareback Shemale Fucks Guy Big Cock Ladyboy
100%
My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
LesFuax 2019-02-16 9,110 first time Small Tits Amateur Latina Bareback Creampie threesome Blowjob Big Cock ass fucking barebacking barebackedshemales first time with a tranny raw anal raw dick raw fucking firsttime
50%
a diary piece - my next date
A diary piece - my next date I hadn't forgotten how to please a man and I had decided to be a little whore for him. Yes I enjoyed it very much and wanted to be fucked again the next day. When I start having sex I want it all the time. HiltonP had said he wanted a date again on 21st and 28th ... Read full Story
amberdoll 2020-09-16 2,633 Stockings Small Tits Crossdresser Amateur Bareback blonde Lingerie Homemade
83%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 5,112 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
80%
TG Girlfriend moves in (part 2)
My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... Read full Story
Jon Paul 2022-01-21 3,452 Big Tits Cumshot Bareback Creampie threesome Blowjob Shemale and Girl Guy Fucks Shemale
100%
Tasting the good FLESH
I am no longer Virgin, en bon et du forme Thing never dared since I taste the enjoyment by all the senses and in all its senses... I discovered her when she smiled at me as a thank-you for giving her the way to the small-town supermarket where I was on business. Sandals at her feet of Cinderell... Read full Story
hippocampus_171 2022-11-10 4,819 Amateur Creampie Shemale Fucks Guy Guy Fucks Shemale Mature Ass to Mouth cum in mouth
50%
A Fantasy - Part 3
Sharon put her cell phone back into her purse, turned to Paula and I and said "I'll be right back, with the Chinese food!", gave us a wink and took out her wallet, grabbed some money and then went off to get our dinner. Paula was sitting on the floor, she leaned back on her left elbow and started... Read full Story
swollenrooster 2023-09-20 5,272 Group Sex Cumshot Shemale Fucks Guy Fetish gangbang Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
50%
An alumni gathering like no other
An alumni gathering like no other; Sea/Sand/Sun' and why not 'Sex' in a vancancy club; we got together to celebrate the 40th anniversary of our 1st meeting at university. The only rule was to come without a partner to relive our 'frosh' days. with friends of whom I had lost all trace, a... Read full Story
hippocampus_171 2024-06-13 1,447 anal Amateur Masturbation Blowjob Sex Toys Mature small cock big ass Ass to Mouth cum in mouth
78%
First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
bigtranslover 2011-05-21 14,979 first time shemales interracial sex
82%
My shemale weekend
I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... Read full Story
shemale lover 2015-09-05 9,455 shemales Group Sex interracial sex
75%
Virginia’s Luxurious Evening
West Palm Beach didn’t have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design’s building overlooking the Intra-coastal Waterway. She had been chilly all day, m... Read full Story
shemale lover 2017-07-16 10,978 tranny Big Cock fingering
100%
The Boy and the Fairy
Local folktales warned of Fairies, but such stories were long ignored or thought of as just a source of amusement. It was after all the twenty first century, mythological creatures were almost entirely forgotten in Dagsdown. But that didn't make them any less real. Since the age of five, Gregory ... Read full Story
shemale lover 2011-09-13 3,415 Small Tits Cumshot handjob
83%
Attitude Adjustment
Angel sat on a chair in a crowd of women. She had come to this club to take in a couple of shows and she was really enjoying this one! This show was a group of hot looking guys that stripped for a living, which is nothing unusual in Miami, but these guys showed the "Full Monty", or in othe... Read full Story
shemale lover 2011-10-24 5,667 asshole Creampie Big Cock
50%
How My Wife Became a Swinger
Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... Read full Story
shemale lover 2011-11-13 5,190 Group Sex Cumshot sucking doggy style
71%
Caught by my wife
I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and... Read full Story
shemale lover 2011-12-07 4,483 first time shemales Group Sex
100%
Catching up, last evening, a date at last
After I moved to France I was too busy to do anything about finding somebody to have fun with – just life getting in the way. I had a date with a post-op ts woman when I went back to the UK in 2008 but since then, no dates. Last year I decided to do something about it so went online and found ... Read full Story
shemale lover 2012-01-09 2,339 hardcore Group Sex cum
100%
His teacher, The transsexual
Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't a... Read full Story
shemale lover 2012-01-31 9,747 shemale Big Cock teacher
100%
The Invitation
"You see, we have to come up with something that would be so embarrassing for you that there is no way that you would ever show those pictures of me to anyone, regardless of how d***k you got, or how horny you got or how pissed off at me you were,” Sally went on. “Something that wou... Read full Story
shemale lover 2012-03-20 6,089 Group Sex crossdressing feminization
95%
Three for Fun
I was on my way home from the bar one night when I noticed a group of ladies standing on the corner talking. As I approached one yelled, “hey sexy looking for the time of your life?” I stop for a minute and stare at the three beauties in front of me. “Well the time of my life does ... Read full Story
shemale lover 2012-03-26 7,070 Big Cock oral sex cum swallowing fisting
100%
A New Dawn Chapter 4
After their little escapade in the office toilets, Tom and Dawn had decided to be a bit more careful at work. As enjoyable and exciting as it had been for both of them, it wasn't worth risking their jobs over. Besides, it just meant that it was all the more pleasurable when they finally got home tog... Read full Story
shemale lover 2012-03-31 3,392 Group Sex Cumshot oral fingering
100%
The Boy is A Girl Now
When I turned 16, I decided to go to a gay bar to see what the deal was. I had not been with anyone ever but I was curious and very much feminine. I stole my older brothers ID and caught the Bus to go to the Ballgame, so I told my mom. Then I wound up at the gay bar just as they opened that night at... Read full Story
shemale lover 2012-05-09 3,703 anal Group Sex sucking rimjob
100%
What If My Mom Part 2
Peggy and Me We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute" Just as Mom left Peggy rolled onto her side facing... Read full Story
shemale lover 2012-06-23 4,622 shemales taboo Group Sex
100%
A Visit To The Booths
I walk nervously into the booths area. My heels clacking on the floor, as I enter the darkness. I pull my dress down, as its already riding up my ass. There are a few men waiting in the first hallway, checking me out as I walk past. I smile and head into the bigger area around the corner. There are ... Read full Story
shemale lover 2012-07-20 3,689 anal sex Group Sex crossdressing facefucking slut
100%
You Keep Them (You’ve Earned Them)
"Stretch, two, three, four" the television commanded. "Up, two, three, four; down, two, three, four," relentlessly. I tried hard to follow. The alarm had gone at seven thirty and I'd been to the bathroom then come back for the work-out. But this one seemed to be designed for p... Read full Story
shemale lover 2012-08-18 4,146 Big Cock fingering handjob
50%
Discovering Mistress Sarah's World Part 5
Chapter 13 Sinking Deeper Into The Feminine World *** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization i... Read full Story
shemale lover 2012-10-03 3,696 Group Sex oral fingering domination
100%
Driving Miss Michele
Michele drove carefully through the cold wet dark streets. She was not used to using the accelerator and brake pedals of her compact sedan in high heels and she was debating whether to pull over and unbuckle the strap of the high heel on her right foot and kick it off. She didn't want to bring atten... Read full Story
shemale lover 2012-11-30 6,560 Group Sex sucking Sex Toys
75%
Find That Guy: Porn TV's TG Gameshow
Freddy was nervous as hell. His girlfriend Sue had signed them up for this stupid game show without even telling him. He still wasn't sure why he'd agreed. Sure they could win a lot of money, and they'd each get a grand just for participating. And sure they needed the money pretty bad. Desperately a... Read full Story
shemale lover 2013-03-04 4,595 sucking Big Cock jerking ass fucking big boobs
93%
SHEMALE SEX IS THE BEST
I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... Read full Story
shemale lover 2014-03-07 4,709 tranny Big Cock ass licking doggy style big boobs rimming
90%
2nd Shemale experience
All my stories are based on my own experiences After my first experience with a shemale (also pasted on here, She was a He) I wanted to have a second, but this time for me to knowingly know what I was about to do. I trolled chat rooms and dating sites for a few months, getting to know a few gi... Read full Story
shemale lover 2014-07-17 3,959 Small Tits Cumshot shemale Lingerie cum swallowing
95%
Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
Ginger__57 2018-03-26 8,609 Stockings gangbang redhead domination Guy Fucks Shemale Ass to Mouth cum in mouth
72%
Alex pt.2
I could not believe it, me and Alex exploring each other's mouths with our tongues. As I pulled Alex closest to me, I could feel a little nub poking what are spandex. Immediately, that made all the blood rush to my cock. Indeed, Alex felt my man meat get hard and big, even more, Alex let out ... Read full Story
Mike212 2018-06-06 3,959 Teen (18+) Small Tits Amateur Big Cock Ladyboy cum in mouth
95%
Mai
When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... Read full Story
Zöe from Kingston 2018-08-09 11,330 Cumshot Bareback Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale Interracial cum in mouth
90%
Long weekend at work
So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dar... Read full Story
Zöe from Kingston 2018-08-09 5,969 Cumshot Bareback Shemale Fucks Guy Blowjob cum in mouth
83%
Janine awaits
My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... Read full Story
bunny cat 2019-02-04 3,801 Crossdresser Masturbation Blowjob Lingerie Mature cum in mouth
100%
My First Experience
Preface: A few years ago I was surfing craigslist (back when that WAS a thing) and found a couple looking for a man. I responded to that post and went back and forth until we set up a time to play. I arrived on the night and had a few drinks, We chatted and I noticed that the husband kept touchi... Read full Story
rileystar 2020-04-01 19,165 Crossdresser Amateur Group Sex threesome Lingerie domination
87%
TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
SpankydeBautumn 2021-02-22 3,836 Crossdresser Amateur Group Sex Cumshot Fetish threesome Blowjob Ladyboy Lingerie Shemale and Girl cum in mouth